Lessons from an Introvert: How to Push Your Limits and Overcome Uncertainty

If you want to achieve any sort of growth in life, you’re going to have to put yourself in uncomfortable situations. Experimentation is the fastest path towards experiences that allow you to learn, develop, and push your limits. Whether new skills, tactics, or techniques – growth comes from change.

But it’s easier said than done, especially for introverts. My perfect day is designed around routine, which helps build discipline and focus. I reserve high productivity times of the day for reading, writing, and creating. Although it’s challenging work, it’s a familiar challenge. It doesn’t generate the same type of discomfort for me as something like public speaking or learning a new skill.

If I’m not careful, it’s easy for me to settle into my comfort zone and ignore uncomfortable opportunities for growth that fall outside of my norm. I have a tendency to take discipline past the golden mean and become too rigid, losing flexibility in my day-to-day. To combat this, I have to disrupt my routine on occasion to make sure I’m still focused on the right things and challenging myself in new ways.

A few weeks ago, after months of deliberation, I shadowed an acting class. I wasn’t sure what to expect–it took everything in me just to show up. I have no desire to be an actor and there’s no hidden talent buried within me. In fact, the thought of acting makes me want to curl up and die. So what was I doing there?

My primary motivation was using it as an experiment to improve my public speaking skills. I came across the idea over coffee with a friend and fellow writer, Lily Hansen. She told me how her background in acting helped improve her stage presence and presentation skills. It was an interesting angle that I thought worth testing out.

The fact remained, I was nervous and in no way looking forward to the class. But I followed through because it aligned with an area of my life that I wanted to improve. The acting class was a vote for my desired identity – not as an actor, but as a stronger communicator and storyteller. I looked at it as an opportunity to arm myself with techniques to build greater comfort presenting in front of an audience.

Everyone’s different, but as an introvert, the question remains – when the stakes are at their highest, how do you take the leap and overcome uncertainty? This is how I’ve learned to navigate that anxiety.

Escaping the narrative

It’s important to know your tendencies. Understanding introversion and extroversion is an important part of self-discovery and awareness. It can help you discover where you gain energy and where your limits are. If you know which way you lean, you’ll know yourself better – when to push and when to ease off.

But keep in mind, it’s a spectrum. There’s a difference between awareness and over-identifying. Humans are incredibly complex. Neatly defined categories are only enticing because they’re easy and allow you to avoid navigating the gray area that defines most of life.

Don’t lock yourself into some narrative you can’t escape. Otherwise, it becomes an excuse to avoid uncomfortable situations. The same goes for extroversion–discomfort means different things to different people. If you want to avoid it, you can find plenty of familiar excuses within your comfort zone.

The power of ”who cares?”

Once you’ve escaped the narrative, it’s about taking the leap. Whether a presentation, high-stakes situation, or looking ridiculous when you’re learning a new skill, how do you take the first step?

When Shaun White, legendary snowboarder and three-time Olympic gold medalist, is at the top of an important run, the last thing he tells himself before he goes off is “who cares.” He doesn’t psych himself up or blast Eminem. He knows he’s put in the preparation. At that point, what happens, happens.

You don’t take new risks or perform your best by fueling your nerves. The who cares mindset isn’t about apathy, it’s about a state of relaxed concentration. This is where you do your best work. It’s a strangely empowering self-talk that helps navigate fears of judgment, failure, or general anxiety about drawing attention to yourself.

When I’m about to do something new or uncomfortable, this mindset provides a moment of calm before the storm. I know I’ll probably look like an idiot (the acting class), but if there’s anything I’ve learned, it’s that most people are too preoccupied with themselves to remember you tomorrow. You’re the only one still thinking about it.

Swim lessons and my life’s finest moments

At twenty-two, after graduating college, I decided to take swim lessons to learn proper technique. I was just getting into triathlons, which necessitate swimming with efficiency unless you want to smuggle in water wings. So I signed up for a month of private lessons at the Vanderbilt aquatics center.

I was prepared to look like a dumbass, but it surpassed even my expectations. The aquatics staff was so accustomed to elementary children signing up for these lessons that they ignored the form I filled out. To their surprise, a grown man, fifteen years older than every other person in the pool, wandered in for lessons.

With seven-year-olds in the lanes to either side, I started my lessons. The instructor (also younger than me) had to come up with a plan on the fly – diving for pool rings in the deep end wasn’t going to cut it. To make matters worse, I couldn’t make it down and back without flailing for air. Overall, these were some of the finest moments of my life.

But the who cares mindset helped me get over my ego and commit to learning proper technique. I looked like a complete noob for the first week, and I was. But with practice and time, I improved. Eight years later, I’m still swimming every week.

I reminded myself of this experience in my anticipation leading up to the acting class. Many of life’s most rewarding experiences happen once you let go of your fear of looking like an idiot. Don’t let your ego hold you back. These people aren’t going to remember you. Show up eager to learn and follow through on what you came to do.

Handling nerves in the moment

Almost always, I find that once I jump off and settle in, my nerves calm. But there are still moments when I get nervous in the middle of a challenging situation or new experience. When that happens, instead of amplifying my focus on myself and fueling my nerves, I shift my attention to externals.

In presentations or high-profile meetings, for example, I focus on non-verbals in the audience or the talking points of other people in the room. This helps keep me from spiraling or thinking ten lines ahead. By focusing outside of myself, I’m able to bring my attention back to the room, settle into the moment, and trust myself.

The All Blacks, New Zealand’s most successful rugby team, have a similar technique they use to bring themselves back to the match and avoid allowing the magnitude of the moment to overcome them. They use breathing techniques to put themselves in a clear, calm state. Then they anchor that state to a specific physical action – scrunching their toes, stamping their feet, or throwing water over their heads. This helps bring them back to the situation at hand and a relaxed state of concentration.

If you get too far ahead in what you’re trying to say or do, you’ll only compound the issue. Instead, come back to now. Project and focus more of your attention outside of yourself. It might be the opposite of your initial instinct to turn within, but it’s far more effective.

Jump when others retreat

If you want to become the best version of yourself, you’re going to have to put yourself out there. Growth comes from pushing your limits, experimenting with different approaches, and learning new skills. The greater tolerance you build for discomfort, the further the reaches of your comfort zone will extend. But this is a lifelong effort.

If you build self-awareness and maintain perspective leading up to, and during, the moment, you’ll be well on your way. Avoid over-identifying, be willing to look like an idiot, and avoid projecting too far into the future. This is how you get out of your own head, take risks, and jump when others retreat to familiar surroundings. It’s here where some of life's most valuable experiences are found.

The Two Sides of Discomfort

Last week, after months of deliberation, I shadowed an acting class. I wasn’t sure what to expect–it took everything in me just to show up. I have no desire to be an actor and there’s no hidden talent buried within me. In fact, the thought of acting makes me want to curl up and die. So what the hell was I doing there?

For those committed to personal growth, discomfort is considered a positive. And it often is. But discomfort can signal different things.

Sometimes discomfort is a sign that you’re growing and pushing the boundaries of your comfort zone or current abilities. Other times it acts an alert, warning you of a misguided decision.

The same concept holds true for exercise. There’s a discomfort that you push through to build strength or endurance. But there’s also a discomfort that signals injury. If you attempt to push through the latter, you compound the mistake and end up worse for it. While exercise is based more on feeling and experience, personal growth shares similar elements.

A certain level of stress is important. As Nassim Taleb, philosopher and writer, explains in his book Antifragile, “Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty.” The key is finding the right threshold.

Wind extinguishes a candle and energizes fire. Likewise with randomness, uncertainty, chaos: you want to use them, not hide from them. You want to be the fire and wish for the wind.
— Nassim Taleb

What’s worth sticking out?

Whenever I’m in an uncomfortable situation, I apply the same rule of thumb that I use to evaluate whether or not something is worth quitting.

I start by asking myself, “Do I feel nervous or uncomfortable because this is difficult? Or do I feel nervous because something’s off and this contradicts my character, values, or principles?”

The former is worth sticking out because that’s where personal growth stems from. The latter means it’s probably time to bow out and reassess.

With the acting class, my primary motivation was using it as an experiment to improve my public speaking skills. I came across the idea over coffee with a friend and fellow writer, Lily Hansen. She told me how her background in acting helped improve her stage presence and presentation skills. It was an interesting angle that I thought worth testing out.

But the fact remained, I was nervous and in no way looking forward to the class. It took a disproportionate amount of energy to even schedule it. But I followed through because it aligned with an area of my life that I wanted to improve.

Another way of looking at this is by using a model James Clear suggests, and asking yourself, “Does this behavior help me become the type of person I wish to be? Does this habit cast a vote for or against my desired identity?”

The acting class was a vote for my desired identity, not as an actor, but as a stronger communicator and storyteller. I looked at it as an opportunity to arm myself with techniques to build greater comfort presenting in front of an audience.

Does this behavior help me become the type of person I wish to be? Does this habit cast a vote for or against my desired identity?
— James Clear

The nuance of discomfort

There’s also a nuance to discomfort that’s worth taking into account. As circumstances change, the type of discomfort can shift beneath you. Earlier this year, a few technology companies reached out about open positions. I went through with the interviews–nerves and all–because I knew they would help me hone my skills, clean up my thinking, and explore my options.

But when it came to an offer, it was a different type of discomfort. I was able to step back and identify that my hesitation was because it didn’t line up with my priorities for the immediate future. I was still more excited about my current team, our upcoming challenges, and what we were building.

In that context, the decision to leave such a positive situation seemed foolish. I didn’t want to jump at the first new opportunity I came across, I wanted the right opportunity. And that meant doubling down on my current position.

The difficult part is that you have to preserve a deep sense of awareness to avoid rationalizing decisions beyond all recognition. There will be moments when you fail to rise to the occasion. Your natural instinct will be to seek out evidence to affirm you made the right decision–confirmation bias.

But life is rarely as neat and orderly as you might hope. You won’t always know, beyond a shadow of a doubt, that you made the right or wrong decision. You just have to assess things to the best of your ability and learn along the way. With greater awareness of your cognitive biases and what discomfort means in different contexts, you’ll be able to make better decisions.

Growth and self-preservation

If you take an impulse at face value, you’ll never be able to differentiate between the shades of discomfort. Consider what side of the spectrum the discomfort you’re facing falls on. One leads towards growth and the other self-preservation.

There will be moments when you’re uncomfortable. That’s not always a bad thing. The vast majority of us would be better off with more adventure, discomfort, and randomness in our lives. But you have to know the difference between stupid risks and opportunities for growth.

If it aligns with your character, it’s worth pushing through those difficult moments when you feel like quitting. No matter how uncomfortable you might be. It’s the discomfort from situations that contradict your character or priorities that deserve a second look.

What Your Painfully Slow Hiring Process Says About Your Product

A few years back I interviewed for a product role with an event management company. The beginning of the process was typical – I visited their local office for three hours of initial interviews, followed by another three hours of virtual interviews with their San Francisco office.

At that point, the fit was a maybe on both sides. And if it’s a maybe after 10 hours of interviews and preparation, that means it’s a no.

Instead of either of us calling it what it was, the company requested that I complete a four-hour homework assignment to gather just a bit more information. The circus continued with dozens of texts, emails, calls, and another on-site interview. And finally, I was extended an offer.

While I should have drawn the line before the homework assignment, the indecision on their part gave me a more accurate understanding of their product development approach.

How you hire reflects how you build

How you hire your product team reflects how you build product. Slow, timid, and scavenging for just one more piece of information? Or knowing what’s critical, pushing forward, and making the best decision based on the available information?

There’s always going to be uncertainty and risk involved in hiring, just as there is in building product. But it’s the amateur product teams who spend weeks agonizing over decisions, failing to account for the value of time.

During interviews, if you experience tactics intended to stall or an exaggerated struggle to make decisions, there’s no reason you should expect anything different in how the product team operates.

I turned down the offer, despite the sunk cost, because of the worrisome parallels. You can tell a lot about product leadership based on the quality of communication and the speed of decisions.

This was one of the determining factors I used to evaluate my current position. It was a no bullshit interview process – the best I’ve ever been a part of. And the hiring process on our product team has proven to be an accurate reflection of our approach to product development.

What does your hiring process say about you?

Consider what your hiring process says about you and your team. If you’re drawing out your interviews for weeks, you’re likely asking the wrong questions or afraid to call a “maybe” what it is, a no. Instead, determine what you’re looking for, move quickly, and operate with conviction (strong opinions, loosely held).

For a better starting place, seek out high-integrity, curious people who add diversity of thought to your existing team. Questions should be geared around this, as well as some combination of analytical skills, creativity, cross-functional experience, and leadership.

And when you’re on the other side of the interview, consider the product, culture, and growth. But don’t give a free pass on the hiring process. If you look close enough, you’ll catch a glimpse of how the product is actually being built.

The best product teams know what they’re working towards – in both their day-to-day and hiring. They’re able to identify what matters, push things forward, and make quality decisions based on the available information. Seek out, and aspire to build, product teams who demonstrate this in every aspect of their work.


*This article was originally featured on Mind the Product

Forget Your Purpose, Start with Meaning

The stories we hear of the successful often make it seem like they were destined for greatness. They identified their purpose from an early age and forged ahead, cutting down distractions in their path. But if you peel back the facade, few encountered sudden revelations. Purpose is hard won.

Child prodigies like Mozart or Tiger Woods are the exception. Robert Greene, best-selling author, worked dozens of jobs as a construction worker, hotel receptionist, translator, and screenwriter, before pitching his first book, The 48 Laws of Power, at age 36. But each step gave him a greater sense of meaning and direction on his way towards writing full time.

It’s human nature to crave a sense of direction. And direction comes from purpose, identity, and authenticity, each of which are intertwined. But they’re not the same thing. If you want to make progress, you have to be able to separate these and lower the stakes. 

Meaning is what purpose is made of

The trouble with taking on purpose from day one is that it appears insurmountable. When you break it down into its individual components, it’s easier to pursue. Purpose is the series of pieces you find meaning in. 

Your life doesn’t need a single purpose out of the gate. Just as it doesn’t need a single meaning. Meaning is an ebb and flow that tracks the motion of your life. If you follow this, it leads towards things you are uniquely suited to bring to life. 

Charles Darwin (1809-1882) discovered botany only after dropping out of medical school. And he wouldn’t publish his theory of evolution until twenty-four years after his visit to the Galapagos Islands. During that time, he speculated on diversity in the natural world through experimentation and careful observation–breeding pigeons, studying barnacles, and soaking seeds in salt water to see how long they survived. What tied together these seemingly unrelated experiments–where he found meaning–was working to understand the nature of life.

Purpose becomes attainable once you stop obsessing over it and turn your attention to the little things you find meaning in on a daily basis. Meaning is within reach.

What’s meaningful to you?

As you seek meaning in your day to day, there are different strategies worth considering. Robert Greene suggests a three-part approach in his book, The Laws of Human Nature.

  1. Consider inclinations in your earliest years – moments when you were unusually fascinated by certain subjects, objects, or activities. 

  2. Reflect on moments when certain tasks or activities felt natural to you.

  3. Determine what particular form of intelligence your brain is wired for (mathematics, logic, physical activity, words, images, music).

Do more of these things. The key is determining what’s meaningful to you and not absorbing what’s important to someone else as your own. Otherwise, you’ll miss the mark. If Darwin listened to his father and remained in medical school, he wouldn’t have joined the crew of the HMS Beagle or discovered the theory of evolution.

And this is perhaps the most difficult skill of all–sorting through the noise and determining what’s your own. It requires years of exploration, introspection, and reflection to determine for yourself. But this exercise gives you a solid start. 

The long game and force multipliers

When you focus on meaning first, you create a system that favors an action-oriented approach. You shift your mental framework from external to internal–what’s within your realm of control. And this is the mindset you need to play the long game. 

The purpose of setting goals is to win the game. The purpose of building systems is to continue playing the game.
— James Clear

The promise of recognition or reward can carry you for days, maybe months. But not years. Only meaning provides that. Robert Greene’s latest book, The Laws of Human Nature, was the culmination of his life’s work and took six years from start to finish. You can’t fake 72 months of sustained effort without turning things back to what’s within your control and finding a stronger sense of meaning in your daily work. 

Aspiring to win a Royal Medal or become a bestseller can still be productive, if held in perspective. But if that perspective is lost and your self-worth becomes dependent on external validation, you’ll likely give up at the first sign of criticism or apathy–and there will be plenty. 

I find meaning in reading, writing, articulating complex problems, leveraging technology to simplify (rather than overcomplicate), and using storytelling to reveal something to people about their own lives. I can sustain each of these indefinitely because they’re meaningful to me and how I make sense of the world. If recognition comes along the way, I’ll welcome it (always keep the upside). But I also won’t stake my existence on it. 

The catch is that few reach achievement without first pursuing meaning. You can get lucky and reach the top once, but to sustain at that level, like Darwin or Greene, requires something more. Meaning is a force multiplier. The stronger the connection to your work, the more force you’ll be able to exert. 

It’s almost impossible to beat someone who’s engaged, finds meaning in their work, and is committed to the long game. 

You still have to determine what you want out of life, make sacrifices, and focus on a few important things. But it’s not worth agonizing over the search for a single purpose from day one. 

Instead, look for the pieces you find meaning in. Trust yourself. Discover ways to blend your unique abilities, interests, and experiences. With dedication and reflection, you’ll discover a sense of purpose that ties it together along the way. 

Inverting the Distraction of Social Media

There are plenty of articles out there that rail against social media. The trouble is not that they’re inaccurate–most hold valid points. It’s that they’re often a laundry list of complaints without any real takeaways, other than “social media sucks” or “regulate Facebook.” At best, you get a call for moderation. 

A more effective approach is to invert the problem. How does the ever-present distraction that is social media present an advantage for you?

Most people aren’t going to dedicate their time to reading, writing, creating, training, or reflecting. Each of these are difficult things to do. It’s much easier to turn to Snapchat or Instagram as a crutch to waste away the hours. 

If you train yourself to do the difficult work that others avoid and ignore the distractions that others can’t resist, you put yourself years ahead. 

But this requires mental toughness and an ability to suffer. Most people panic at the first sign of discomfort. You’re sacrificing immediate for delayed gratification. If you’re able to master this impulse and embrace discomfort, you provide yourself more opportunities for growth. 

We distinguished the excellent man from the common man by saying that the former is one who makes great demands on himself, and the latter the one who makes no demands on himself…
— José Ortega y Gasset

In the age of distraction, there’s no greater differentiator than establishing yourself as a stalwart of focus and creativity. 

This comes from allowing yourself to sit with something, even if it means getting stuck. Nail Gaiman, author, uses a similar technique when he sits down to write. He gives himself permission to either write or do nothing. But everything else is off the table. Sooner or later, staring off into the distance gets boring and the only alternative is to write. 

In many ways, distractions are a training ground. Social media is just the latest culprit. If you’re able to resist the easy thing within reach and focus instead on the more challenging task, that translates across every aspect of your life. 

Most people think they can wait around for the big moments to turn it on. But if you don’t cultivate ‘turning it on’ as a way of life in the little moments – and there are hundreds of times more little moments than big – then there’s no chance in the big moments.
— Josh Waitzkin

You can either complain about the distraction that is social media or you can use that energy to turn in to your advantage. And it’s a tremendous advantage for those able to ignore the noise and create more

Are you going to sit down and do the work? Or are you going to be a sucker for another quick hit of empty recognition that comes from someone mindlessly scrolling through their feed and tapping on your status? 

Let other people wander towards distraction. Social media should be just another test to hone your focus and practice tuning out the noise. 

The more time you spend creating, the more fulfilled you are going to be. History belongs to those able to overcome the incessant distractions of their time. 

More Action, Less Talk

In May of 2009, I was finishing up my sophomore year at Indiana University. Without an internship lined up, I decided to dedicate most of the summer to writing and recording music. That was my path towards perceived significance and I had an ego to match it. 

When one of my friends signed up to lead music at a summer camp in Northern Minnesota for the entire month of June, it was an easy decision to tag along. I used it as an excuse to get away from home and focus on music. I also knew a handful of other people volunteering. One of the camp leaders, Jon, was a mentor and close friend. 

Before leaving for the trip, Jon and I met for lunch. We talked about how excited we were to spend a month together in Minnesota. He also mentioned how he couldn’t wait to hear the music each night. But he had one recommendation, “Keep it quiet…don’t walk around promoting how you’re a musician to other volunteers or campers. Just let people find out for themselves.”

It’s easy to glance over this at a surface level. But it was a profound lesson for a twenty-year-old, self-assured musician. This was the first lesson I learned in navigating ego. And it’s one I’ve continued to visit on an almost daily basis since.

More action, less talk.

With close to a decade more experience in life, Jon saw straight through my shit. But the way he approached it is what made the difference. He could have shrugged me off as an “idiot teenager” or come down with sharp criticism, causing me to shut down. Instead, he led an open conversation and explained one of life’s most important lessons–especially for those doing creative work. 

When you reveal less up front and people discover something interesting about you later on, it builds intrigue. You demand far greater respect than if you volunteered that same information unsolicited. It also adds a layer of depth and authenticity that draws people in.

I would much rather have men ask why I have no statue, than why I have one.
— Cato the Elder

Action outweighs talk. This approach lends you far more credibility. Those who self-promote and overshare at every chance lose the force behind their voice. It becomes noise, lost to the wind.

People don’t need to know everything about you. In an era that’s obsessed with social media and vulnerability, it might seem counterintuitive. But the less you talk about yourself and the less you reveal up front, the more it draws people in. 

The world gravitates towards depth. Not shallow plays at status and virtue signaling.

Silence is a form of absence and withdrawal that draws attention; it spells self-control and power.
— Robert Greene

This is not to say that you should become a hermit and refuse to reveal anything about yourself in conversation. But it is to say that you should use discretion. If you’re able to refrain from oversharing, you provide yourself an opportunity to get beyond your ego. This allows you to actually listen to the person in front of you or shift your focus towards the work that matters.

Live by your principles, not by status. 

Meaningful progress and satisfaction come from deep work and realizing your own potential. In my case, it came from the music itself. And now it comes from quiet moments of writing. It’s the creative process that keeps me going. And I know I can sustain that indefinitely. It’s independent of the fleeting highs of recognition.

Pursue the things you love, create meaningful work, and let people find out on their own terms. Whatever you have to say will be far more effective when you’re not using brute force to get your message across. 

The further you can distance yourself from your ego or your obsession with personal brand, the greater respect you’ll demand. More action, less talk. Reveal your depth little by little. That’s how you draw people in, build lasting relationships, and create something that strikes a deeper chord in others. 

And for God’s sake, please don’t walk around telling people you’re a singer-songwriter.

Indecision in Product: How to Avoid Becoming a Bottleneck

A few years ago, comedian Aziz Ansari released a Netflix special called “Live at Madison Square Garden”. During his set, he joked about the effort required to buy a new toothbrush. Not just any toothbrush would do, he had to have the best. He researched for hours, Googling “best toothbrush” and reading articles on the pros and cons of bristle strength. As he reflected, he questioned his indecisiveness and his desire to have the best when any toothbrush would have done the job.

For most of my twenties, I did the same thing. I researched every purchase – headphones, winter jackets, coffee grinders – in painstaking depth before making a decision. But, as I’ve learned, the quest for a perfect decision often does more harm than good.

Time is far more valuable than a marginally better solution. And if you’re leading product, the sooner you learn this lesson, the better. As a product manager, the worst position you can put yourself in is creating a bottleneck by making slow decisions.

A Case Study in What Not to Do

When I started my career, I joined a team building a web-based patient portal for healthcare providers. At the time, I was unaware “product” even existed. But I was forced to learn the space out of necessity. My first manager, Eric, was a walking case study in how you shouldn’t handle product decisions.

With something as simple as our landing page, Eric went back and forth for months. His opinion fluctuated on a daily basis. Without the autonomy to make decisions, our development team wandered without any real sense of direction or progress.

Each week followed the same pattern. The team would align on the problem, collaborate on ideas, prioritize features to build and test, then have the tables turned on them a few days later. Eric was obsessed with surveying every available option. He operated with the constant fear that we might have missed something better. As a result, we wasted months of time and energy considering alternatives with negligible differences.

And if we were unable to make decisions on something as simple as the landing page, imagine what that did to our product which was heavy on integrations with practice management and electronic health record systems. Not to mention the most important piece–the user experience of patient-facing features.

The lesson: hesitation kills creativity, morale, and momentum.

Be Wrong as Fast as You Can

Leaving your team in limbo without a sense of direction is a far worse position to be in than taking a wrong step. It’s easier to forgive a wrong decision than it is a painstakingly slow decision or the failure to make a decision.

For extraordinary outcomes, seek conviction in your work and build teams that value conviction over consensus.
— Scott Belsky

If you’re wrong, you want to be wrong as fast as possible. Andrew Stanton, director at Pixar, uses a similar model to evaluate decisions on his films. When faced with two hills and you’re unsure which to attack, the best course of action is to hurry up and choose. If you discover it’s the wrong hill, you can always turn around and attack the other. But you will fail for as long as you continue standing still or running in between the hills.

There will be things you miss and ideas you haven’t thought of. But you’re going to learn more by putting yourself and your product out there than you will trying to make the perfect decision each step of the way.

How Reversible Is This Decision?

For many product managers, faster decision making is the most significant improvement you can make. Especially when it comes to the trivial.

While somewhat elementary, the Pareto Principle should be foundational to your decision making. Which solution generates 80% of the value? Forget the other 20%. As Aziz points out in his toothbrush dilemma, perfection requires far more deliberation and research than it’s often worth. If your default position is hesitation – pausing to consider every alternative – you’ll stifle creativity and lose your team along the way.

You can also make immediate improvements by asking yourself a single question, “How reversible is this decision?” Tobi Lütke, Shopify’s founder and CEO, uses a similar strategy by asking himself, “How undoable is this decision?” Decisions that are reversible – most of the ones you make on a daily basis – deserve quick answers.

Better yet, if you have other product managers, developers, or designers coming to you with trivial decisions, empower them to make the call. Performance will improve when there’s a greater degree of autonomy and teams have more creative control over the product.

The decisions that aren’t easily reversible are the rare ones that Lütke spends his time deliberating before coming to a decision. In 2008, he had to decide whether Shopify would remain the lifestyle business he set out to build or shift towards a growth company. With venture capital implications, it warranted thoughtful consideration.[1]

Slow, deliberate decision-making can be a significant advantage in avoiding massive mistakes. But the reality is that most decisions you have to make on a daily basis aren’t permanent in nature. There’s a time and place to use this level of deep thought and consideration. Not when it comes to buying a toothbrush or choosing between two styles on a landing page.

Far too many product managers are focused on perfection from day one – an impossible task. Instead, with proper context, you should focus on making faster decisions. You’ll always be able to adapt along the way as you learn.

If you want to avoid becoming a bottleneck, just keep things moving forward. You’ll be better for it, your team will be more engaged, and you’ll be able to build better products. Decisions lead to progress because they improve the rate at which you learn.

Both life and product become much easier when toothbrush decisions aren’t monumental efforts. Learn to value your time over a marginally better solution. People appreciate decisiveness. And above all, that’s the sign of a true leader in product.



[1] Lütke still felt like he was far too slow in coming to this decision (lifestyle vs growth). To help speed up bigger decisions, he now tries to get as far ahead as he can in terms of vision and where the company is heading. In other words, being less reactive to inevitable, significant decisions that need to be made.

*This article was originally featured on Mind the Product

The Power of Your Early Influences

Many of us are embarrassed by our early influences. No one admits to how much they loved listening to Matchbox Twenty, watching Spielberg films, or reading The Hunger Games. Everyone’s too worried about promoting how refined their tastes are.

But underneath all that virtue signaling, the truth is that your early influences were foundational to many of the things you find inspiration in today. They’re the branches who first led you to the mediums and ideas that resonate strongest with you.

One of the most important influences of my early twenties was author Tim Ferriss (and he continues to be to this day). But because of how many people he’s reached–also known as success–he has his haters. While an aversion to the mainstream might be inherent to high-brow culture, it’s ridiculous to think you’re above your early influences. Without Ferriss, I wouldn’t have discovered eighty percent of the most influential books I’ve read in recent years.

The Branches: Tim Ferriss led me to Derek Sivers, who led me to Nassim Taleb and Stoicism, which led me to Ryan Holiday, who led me to Robert Greene. These are the authors, entrepreneurs, and philosophers who have had the most profound influence in my life over the past ten years. 

Foundational influences matter because they connect us with more specific interests and allow us to explore those in greater depth. For me, Ferriss is brilliant in orchestrating these connections.

The same concept holds true for influences in any other area of interest or field of study. Those who first peaked your curiosity–regardless of reason–helped lay the groundwork for where you are today. If you trace the past decade of your deepest interests, you’ll start to see a map similar to the one above. 

If you’re too worried about virtue signaling and showing off your refined tastes, you’re not only missing the point, you’re actively discouraging others. 

It’s important to allow your tastes to evolve, but don’t dismiss someone who’s just starting out. Allow them the an opportunity to explore on their own without telling them what they should care about. 

Investor and entrepreneur, Naval Ravikant, offers advice for early readers that’s applicable across disciplines, “Read what you love, until you love to read.” People who love to read and dig into books on complex ideas started by reading simpler subjects that resonated with them years earlier. 

You begin based on where you are today and what your natural interests are. Otherwise you don’t learn to love reading (or music, film, sports, finance, international business, teaching, technology). And if you don’t develop a love for reading itself, you’re never going to make it from R.L Stine’s Goosebumps to Nassim Taleb’s Incerto

If you’re too busy feigning interest in what you’re supposed to care about, instead of what you actually enjoy, you’ll kill your natural curiosity trying to keep up with the connoisseurs. 

Your early influences, based on your unique interests, are the ones who help build your latticework of mental models and network of influences. From here you can begin branching out to connect different ideas, authors, concepts, and styles.

Embrace your early influences. The only thing that matters is what resonates with you at this point in your life and what you find inspiration in. It’s okay to listen to a catchy pop song or read a pop-fiction title just because you enjoy it. That’s reason enough. Let the foundation lead the way.

Why the Worst Product Managers Expect the Best

With each product I’ve built, things rarely come together exactly as planned. But it’s not the inconveniences, technical challenges, or misguided people that are the problem. It’s that we ever allow them to catch us off guard in the first place.

Anyone can operate under ideal conditions. But ideal conditions are the exception, not the rule. Eighty percent of your time building product will take place in a maelstrom of ambiguity and obstacles.

It’s naive to expect that the world should bend to your favor and promote ideal conditions. Most reasonable people acknowledge this. But when it comes down to it, many of us cling to expectations that our work should progress without pushback and our lives should follow a neatly charted map. We forget how much of life is negotiating egos and hidden variables along the way. 

The best teams embrace imperfections beyond their control and create great products anyway.

The worst teams self-destruct because they’re too busy obsessing over inconveniences. 

It’s easy to pick out the product teams who struggle with this. Each challenge appears to catch them off guard, demoralizing the team and throwing people into a state of anger or despair. This type of reaction points to two things: inexperience and fragility.

Improvement comes from experience and perspective–you’re prepared to face a wider range of potential scenarios. In turn, this allows you to develop a deeper well of resilience and resourcefulness.

Creativity and resilience

At age 23, I started working for a healthcare startup, building out a web-based patient portal. Each setback caught me off guard because I expected things to just work–a laughable statement for anyone who has worked in technology for more than a week. When I went on-site for the launch with our first big client, I was unable to anticipate the ways I was about to get torched. 

There were technical challenges inherent to a complex healthcare organization and integrations with its existing software that we had to sort through. But the technical challenges were only half of it. The true test was handling stakeholders–internal and external–as well as the people who create noise and thrive on passive-aggressive emails.

Anyone who has worked in product is familiar with these challenges. There’s nothing unique about them. But I struggled to adapt because my expectations were off base. I lacked perspective. I was focused on perfection in our product and people pleasing–both impossible tasks–rather than creativity and resilience. 

The best product managers are able to cycle through dozens of permutations and anticipate certain situations through dimensional thinking. But no matter how good you are, at some point you’ll get hit by something you didn’t see coming. Whether the feature you’ve been working on breaks or a “senior leader” steps in and changes the rules at the last minute, you will encounter situations that test your limits. 

Your job isn’t to prevent these mistakes or eliminate every obstacle. Rather it’s to develop the ability to continue moving forward when the inevitable occurs. Leading product requires that you establish an unwavering sense of perspective and imbue this quality in your team. Then, and only then, can you build the resilience and resourcefulness to adapt, imagine creative solutions, and bring them to life. 

Resilient teams who cause a few more quality issues will always beat out fragile teams who are only able to operate under perfect conditions. The difference is self-awareness and being able to step back to put things in perspective. This means assuming responsibility instead of feeling sorry for yourself because something you built didn’t work or someone criticized you. 

This is not to say that you shouldn’t focus on promoting favorable conditions. You can’t create a complete shit storm for yourself and hope to come out better for it. But you should also understand that you’re never going to get ideal conditions. There are going to be things beyond your control. And that’s what keeps life interesting–the challenges and obstacles you have to learn how to overcome along the way.

Each team meeting, one-on-one, and retrospective is an opportunity to develop these qualities in your team. By challenging each other to maintain perspective and reflect on experiences, you can turn things back to what’s within your control–your attitude, the effort you put into your work, and the guiding principle that propels you forward.

Opportunities for reflection

In my experience, few things are more valuable to the morale and resilience of a team than holding retrospectives every few weeks. These are best done with your immediate team (keep things small so everyone can have their voice heard) in a low-stress environment, outside of work. There are multiple formats, but each person should have a chance to discuss what’s gone well and what hasn’t. 

This provides a valuable outlet for everyone to air their frustrations, without judgment or repercussions, and remind each other of recent accomplishments. It also allows the team to come together and consider how you might frame challenges in a more productive light and course correct the things within your control.

Retrospectives are just one outlet to discuss experiences and rediscover perspective. And with the right perspective, you can begin building the resilience to navigate the conflict and uncertainty inherent to challenging work. 

Creating more opportunities for reflection is the best way to harness experience and build perspective. It’s the first step towards realizing that imperfect conditions are where the majority of life takes place. Knowing this, you’ll be able to lead better teams, build better products, and live a better life. 

Expect challenges. Expect unknowns. Expect ego. When you set your expectations accordingly, you’ll waste less time consumed by the things that have happened to you. 

Anyone can operate under ideal conditions. But the best product teams don’t sit around waiting for the stars to align. Instead, they embrace the imperfections inherent to life, create their own momentum, and make things happen for them. To steal a line from Charles Bukowski, “What matters most is how well you walk through the fire.”



*This article was originally featured on Mind the Product.

Why Your First Bet Is Always Wrong

Why Your First Bet Is Always Wrong

Far too often we fixate on optimizing the first idea we come across. We become emotionally attached to a single design, storyline, or hypothesis. The end result is a slow crawl towards incremental improvement. Our work becomes a shell of how good it could be if it were allowed to evolve.